Fluorine-directed 1, 2-trans glycosylation of rare sugars. Issue 24 (16th February 2016)

• Record Type: Journal Article
• Authors: Aiguabella, Nuria; Holland, Mareike C.; Gilmour, Ryan
• Is Part Of: Organic & biomolecular chemistry. Volume 14:Issue 24(2016)
• Page Start: 5534
• Page End: 5538
• Publication Date: 2016-02-16
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c6ob00025h
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : To reconcile the urgent need to access well defined β-configured 2, 6-di-deoxypyranose analogues for chemical biology, with the intrinsic α-selectivity of the native system, the directing role of fluorine at C2 has been explored. Abstract : To reconcile the urgent need to access well defined β-configured 2, 6-di-deoxypyranose analogues for chemical biology, with the intrinsic α-selectivity of the native system, the directing role of fluorine at C2 has been explored. Localised partial charge inversion (C–H δ + → C–F δ − ) elicits a reversal of the substrate-based α-stereoselectivity, irrespective of the protecting group electronics.